Aminosiloxane polyether polymers

ABSTRACT

Textiles treated with a textile treating composition containing a silane or organosiloxane containing both an Si—C bonded aminoalkyl group containing a primary, secondary, or tertiary amine group, and at least one Si—O—C bonded (iso) oxyalkyl radical exhibit excellent soft hand while maintaining superior water-wettability.

The invention relates to a textile treatment process which uses acomposition based on aminoalkyl- and (iso)oxyalkyl-containingorganopolysiloxane and to novel aminosiloxane-polyether polymers.

A number of recent patents describe modifications to the polyoxyalkylenechain or to the organopolysiloxane for property optimization for a largenumber of applications. The functional groups and the polyoxyalkylenechains can be linked to the organopolysiloxane by way of Si—O—C or Si—Cbonds.

DE 3928867 describes the use of polysiloxane-polyoxyalkylene blockcopolymers which comprise at least one amino-functional group attachedto a silicon atom in the production of polyurethane foams. Thepolyoxyalkylene group and the amino-functional group can be attached viaSi—O or Si—C. The polyoxyalkylene group and the amino-functional groupcan be located either at the ends or at the sides. The amino-functionalgroup comprises at least two nitrogen atoms, of which that located atthe end must be fully substituted by alkyl groups.

There is no description of polysiloxane-polyoxyalkylene block copolymerswhich comprise an amino-functional group attached to a silicon atom andhave only one nitrogen atom, or of those which comprise two or morenitrogen atoms in the side chain and in which the terminal nitrogenatoms are substituted by at least one hydrogen atom. The use of thepolymers described in DE 3928867 for fibre finishing is likewise notdescribed.

U.S. Pat. No. 5,075,403 and EP-A-0404698 describe apoly-diorganosiloxane having amino and polyoxyalkylene side groups. Thefunctional groups are attached via Si—C. Preparation is byhydrosilylation. The use of the polymers of the invention as wettingagent and dispersant or as additive in fabric softeners or antifoampowders is described.

Si—O—C-attached polyoxyalkylene groups are not described.

EP-A-0579999 describes a composition for defoaming an aqueous,especially alkaline, formulation based on organofunctionally modifiedorganopolysiloxanes and finely divided silica. The organopolysiloxaneused in the formulation is an amino siloxane whose amine groups areconnected to the organopolysiloxane by way of Si—C or Si—O—C bond. Inaddition to the amine groups, the organopolysiloxane may also containpolyether radicals connected to the organopolysiloxane by way of Si—C orSi—O—C bond.

The combination of amino-functional and polyalkylene oxide-containinggroups in the organopolysiloxane is also known. Alkylamine-polyalkyleneoxidepolydimethylsiloxane terpolymers andpolydimethylsiloxaneamino-polyalkylene oxide block copolymers havealready been used for the finishing of textiles (cf. A. M. Czech et al.,“Modified Silicone Softeners for Fluorocarbon Soil Release Treatments”).In that case the polyalkylene oxide groups are linked to theorganopolysiloxane by way of Si—C bond.

A disadvantage of the prior art is that Si—C-bonded polyalkylene oxidegroups are available only by way of the hydrosilylation reaction ofallylpolyalkylene oxide groups on H-containing silanes andorganopolysiloxanes. This process requires relatively expensive rawmaterials and special safety measures, since elimination of hydrogenmust be expected in the case of hydrosilylation reactions. In addition,Si—C-bonded polyalkylene oxide groups cannot readily be eliminated ondemand, as is desired in textile finishing in order to improveexhaustion capacity and permanence.

It is an object of the invention to overcome the disadvantages of theprior art.

A subject of the invention is a process for textile treatment in which acomposition comprising at least one

(A) silane or organosiloxane having at least one monovalent SiC-bondedradical with primary, secondary and/or tertiary amino groups and atleast one

(B) (iso)oxyalkyl radical which is attached via Si—O—C is used.

In the composition, preferably, the silane or organosiloxane (A) has aunit of the general formula (I) $\begin{matrix}{R_{a}^{1}Q_{b}{SiO}_{\frac{({4 - a - b})}{2}}} & (I)\end{matrix}$

and all other siloxane units in an organopolysiloxane have the generalformula (II) $\begin{matrix}{R_{c}^{1}{SiO}_{\frac{({4 - c})}{2}}} & ({II})\end{matrix}$

and have (iso)oxyalkyl radical of the formula

(OC_(n)H_(n)(−R)_(n))_(o)  (III)

where

R can be identical or different and denotes hydrogen or a methylradical.

The (iso)oxyalkyl radicals of the general formula(OC_(n)H_(n)(—R)_(n))_(o) can also be linked to the organopolysiloxaneat one or both ends by way of Si—O—C bonds. The (iso)oxyalkyl radicalsare preferably adducts of polyethylene oxide, polypropylene oxide andtheir copolymers. By altering the polyethylene oxide/polypropylene oxideratio it is possible to influence the stability of the Si—O—C bond tohydrolysis.

R¹ denotes identical or different, monovalent, unsubstituted orfluorine-, chlorine- or bromine-substituted C₁ to C₁₈ hydrocarbonradicals, hydrogen atoms, C₁- to C₁₂-alkoxy or hydroxyl radicals oralkyl glycol radicals,

Q denotes a group of the general formula (III)

—R²—[NR³(CH₂)_(m)]_(d)N(R³)₂  (III)

where

R² denotes a divalent C₁ to C₁₈ hydrocarbon radical,

R³ denotes a hydrogen atom or an unsubstituted or fluorine-, chlorine-or bromine- or C₁- to C₅-alkoxy-substituted C₁ to C₁₈ hydrocarbonradical,

a has the values 0, 1 or 2,

b has the values 1, 2 or 3,

c has the values 0, 1, 2 or 3,

d has the values 0, 1, 2, 3 or 4,

m has the values 2, 3, 4, 5 or 6,

n has the values 2, 3 or 4 and

o has the values from 1 to 100

and the sum of a and b is not more than 4.

Examples of C₁ to C₁₈ hydrocarbon radicals are alkyl radicals, such asthe methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl,n-pentyl, isopentyl, neopentyl, tert-pentyl radical; hexyl radicals,such as the n-hexyl radical; heptyl radicals, such as the n-heptylradical; octyl radicals, such as the n-octyl radical and isooctylradicals, such as the 2,2,4-trimethylpentyl radical; nonyl radicals,such as the n-nonyl radical; decyl radicals, such as the n-decylradical; dodecyl radicals, such as the n-dodecyl radical; cycloalkylradicals, such as cyclopentyl, cyclohexyl, cycloheptyl radicals andmethylcyclohexyl radicals; aryl radicals, such as the phenyl and thenaphthyl radical; alkaryl radicals, such as o-, m-, p-tolyl radicals,xylyl radicals and ethylphenyl radicals; and aralkyl radicals, such asthe benzyl radical, the alpha- or β-phenylethyl radical.

The above hydrocarbon radicals R¹ may comprise an aliphatic double bond.Examples are alkenyl radicals, such as the vinyl, allyl, 5-hexen-1-yl,E-4-hexen-1-yl, Z-4-hexen-1-yl, 2-(3-cyclohexenyl)ethyl andcyclododeca-4,8-dienyl radical. Preferred radicals R¹ with aliphaticdouble bond are the vinyl, allyl, and 5-hexen-1-yl radical.

Preferably, however, not more than 1% of the hydrocarbon radicals R¹contain a double bond.

Examples of C₁ to C₁₈ hydrocarbon radicals substituted by fluorine,chlorine or bromine atoms are the 3,3,3-trifluoro-n-propyl radical, the2,2,2,2′,2′,2′-hexa-fluoroisopropyl radical, the heptafluoroisopropylradical, and the o-, m- and p-chlorophenyl radical.

Examples of the divalent C₁ to C₁₈ hydrocarbon radicals R² are saturatedstraight- or branched-chain or cyclic alkylene radicals such as themethylene and ethylene radical and also propylene, butylene, pentylene,hexylene, 2-methylpropylene, cyclohexylene and octadecylene radicals orunsaturated alkylene or arylene radicals such as the hexenylene radicaland phenylene radicals, particular preference being given to then-propylene radical and the 2-methylpropylene radical.

The alkoxy radicals are above-described alkyl radicals which areattached by way of an oxygen atom. The examples of alkyl radicals applyfully to the alkoxy radicals R¹ as well.

The alkyl glycol radicals R¹ preferably have the general formula (IV)

—R²—[O(CHR³)_(d)]_(n)OR⁴  (IV)

in which R², R³ and d have the above definitions, n has a value from 1to 100 and R⁴ denotes a hydrogen atom, a radical R³ or a group of thegeneral formula —(C═O)—R⁵ where R⁵ denotes the radical R³ or O—R³.

In the above general formulae (I) to (IV), preferably,

R¹ denotes a methyl, phenyl, C₁- to C₃-alkoxy or hydroxyl radical or aradical of the general formula (IV),

R² denotes a divalent C₂ to C₆ hydrocarbon radical,

R³ denotes a hydrogen atom, a methyl radical or cyclohexyl radical,

a denotes the value 0 or 1,

b denotes the value 1,

c denotes the values 2 or 3, and

d denotes the value 1.

Particular preference is given to linear poly-dimethylsiloxanes whichmay or may not have C₁- to C₃-alkoxy or hydroxyl end groups. In thesepoly-methylsiloxanes, Q preferably denotes a group H₂N (CH₂)₂NH(CH₂)₃—or H₂N(CH₂)₂NHCH₂CH(CH₃)CH₂—.

A further subject of the invention is (A) silane or organosiloxane whichhas at least one monovalent SiC-bonded radical with primary, secondaryand/or tertiary amino groups, with the proviso that theorganopolysiloxane contains only M and D units and the amino-functionalgroup located at the end has at least one hydrogen atom and at least one

(B) (iso)oxyalkyl radical.

The (iso)oxyalkyl radicals of the general formula(OC_(n)H_(n)(R)_(n))_(o) can also be linked to the organopolysiloxane atone or both ends by way of Si—O—C bond. The (iso)oxyalkyl radicals arepreferably adducts of polyethylene oxide, polypropylene oxide andcopolymers thereof. By altering the polyethylene oxide/polypropyleneoxide ratio it is possible to influence the stability of the Si—O—C bondto hydrolysis.

The ratio of the siloxane units of the general formula (I) to thesiloxane units of the general formula (II) is preferably 1:10 to 30,000,especially 1:20 to 300.

The weight ratio of polyorganosiloxane to polyoxyalkylene groups is from99:1 to 10:90, in particular from 95:5 to 30:70. The ratio ofamino-substituted Si to total Si is preferably from 1:500 to 1:5, inparticular from 1:200 to 20.

The amine contents of the composition of the invention are preferablyfrom 0.1 to 2 mequiv/g, in particular from 0.1 to 0.7 mequiv/g, measuredas the consumption of 1 N hydrochloric acid in ml/g oforganopolysiloxane A in the course of titration to the neutral point.

It is possible to employ one type of silane or organosiloxane (A). It isalternatively possible to employ a mixture of at least two differenttypes of silane and/or organosiloxane (A).

The silane or organosiloxane (A) or a mixture of at least two differenttypes of silane and/or organosiloxanes (A) preferably has an averageviscosity of from 1 to 100,000 mPa·s, in particular from 1 to 10,000mPa·s, at 25° C.

A further subject of the invention is a process for preparing thecompositions of the invention by using at least one

(A) silane or organosiloxane having at least one monovalent, SiC-bondedradical with primary, secondary and/or tertiary amino groups and aglycol which has at least one

(B) (iso)oxyalkyl radical.

The silanes or organosiloxanes (A) are prepared from

(E) compounds selected from

(E1) organosilanes having at least one monovalent SiC-bonded radicalwith primary, secondary and/or tertiary amino groups and at least oneC₁- to C₄-alkoxy group and

(E2) organosiloxanes having at least one monovalent SiC bonded radicalwith primary, secondary and/or tertiary amino groups and at least oneC₁- to C₄-alkoxy and/or silanol group and

(F) compounds selected from

(F1) organosilanes having at least one C₁- to C₄-alkoxy group and

(F2) organosiloxanes having at least one C₁- to C₄-alkoxy and/or silanolgroup,

(G) glycols of the formula

H(OC_(n)H_(n)(—R)_(n))_(o)OH,

where

R=methyl or denotes H

and also basic or acidic catalysts.

The organosilanes (E1) preferably have the general formula (VI)

Q_(e)R⁶ _(f)SiR¹ _((4−e−f))  (VI)

in which

R⁶ is a C₁- or C₂-alkoxy radical,

e denotes the values 1, 2 or 3, and

f denotes the values 1, 2 or 3, with the proviso that the sum of e and fis not more than 4, and

Q and R¹ have the above definitions.

The organosiloxanes (E2) preferably have at least one siloxane unit ofthe above general formula (I) and at least one siloxane unit of thegeneral formula (VII) $\begin{matrix}{{R_{g}^{1}R_{h}^{6}R^{7}O_{i}{SiO}_{\frac{({4 - g - h})}{2}}},} & ({VII})\end{matrix}$

and all other siloxane units have the above general formula (II),

where

g denotes the values 0, 1 or 2,

h denotes the values 1, 2 or 3, and

i denotes the values 0 or 1, with the proviso that the sum of g, h and iis not more than 3, and

Q, R¹ and R⁶ have the above definitions and R⁷ represents H or a C₁- toC₆-alkyl group.

The organosilanes (F1) preferably have the general formula (VIII)

R⁶ _(j)SiR¹ _((4−j))  (VIII)

in which

j denotes the values 1, 2, 3 or 4 and

R¹ and R⁶ have the above definitions.

The organosiloxanes (F2) preferably have at least one siloxane unit ofthe above general formula (VII), and all other siloxane units of anorganopolysiloxane have the above general formula (II).

Preferably, e denotes the value 1.

The organopolysiloxanes (E2) and (F2) preferably have an averageviscosity of from 10 to 100,000 mPa·s, preferably from 20 to 10,000mPa·s and, in particular, from 50 to 1000 mPa·s at 25° C.

The acidic catalysts are preferably Lewis acids such as BF₃, MgCl₂, andZnCl, and proton-acidic compounds of the halogens, such as HF, HCl, HBrand HI, and sulphur-acidic compounds such as H₂SO₄ and H₂SO₃.

The basic catalysts are catalysts such as alkali metal hydroxides,especially sodium, potassium and caesium hydroxide, alkali metalalcoholates, quaternary ammonium hydroxides, such as tetramethylammoniumhydroxide, benzyltrimethylammonium hydroxide, benzyltriethylammoniumhydroxide, benzyltrimethylammonium butylate,β-hydroxyethyltrimethylammonium 2-ethylhexanoate, quaternary phosphoniumhydroxides, such as tetra-n-butylphosphonium hydroxide andtri-n-butyl-3-[tris(trimethylsiloxy)silyl]-n-propylphosphoniumhydroxide, alkali metal siloxanolates and ammonium organosiloxanolates,such as benzyltrimethylammonium siloxanolate and tetramethylammoniumsiloxanolate.

Use is made preferably of from 10 ppm to 1% by weight, in particularfrom 50 to 1000 ppm, of catalyst, based in each case on the weight ofthe organosilicon compounds employed.

The amounts (E), (F) and (G) result from the required physical data.

Products containing acyl groups can be prepared by using acylatedamino-functional silanes or by reacting the aminopolyoxyalkylenesiloxaneof the invention with acylating reagents, such as carboxylic anhydrides,carboxylic esters, carboxylic acids, lactones and carbonates.

The preparation of (A) takes place preferably at temperatures from 50 to300° C., in particular from 80 to 200° C.

The reaction time within which 99 mol-% of the starting compounds (E),(F) and (G) are reacted to silane or organosiloxane (A) is in most casesfrom 1 hour to 20 days, in particular from 12 hours to 3 days.

In order to avoid reverse reactions it is important in the course of thepreparation to remove from the reaction mixture all eliminationproducts, such as water, alcohol and ethers.

The textile treatment formulations of the invention comprise preferably(A) silane or organosiloxane in amounts of from 1 to 60% by weight, morepreferably from 1 to 30% by weight, and water in amounts from 40 to 99%by weight.

The compounds of the invention can be used as compositions for thetreatment of leather, bonded web fabrics, cellulose, fibres, textiles,nonwovens and tissues, as a constituent of antifoam formulations, aswetting agents, as a coatings additive and as a stabilizer for PU foam.

Advantages are the very good slip effect and outstanding softnesscoupled with very good hydrophilicity, depending on composition, easilyemulsifiable —self-dispersing—soluble in water, depending oncomposition, high liquor compatibility, surprising stability tohydrolysis for forced application from aqueous liquor, and goodexhaustion capacity as a result of targeted partial hydrolysis of theSi—O—C bonds. Furthermore, the compositions of the invention have a goodstability which may amount to years. In addition, the stability can alsobe adjusted through the targeted choice of the glycol and of the pH, thepH preferably lying at from 7 to 9.

PREPARATION EXAMPLE 1

693.75 g of an OH-terminal polydimethylsiloxane having a viscosity of 50mPa·s are mixed with 21.38 g ofaminoethylaminopropylmethyldimethoxysilane, 358.07 g of polyethyleneglycol 400 and a basic catalyst. The result is a turbid whitish mixture.The mixture is heated gradually to 200° C. with stirring, in the courseof which volatile constituents are removed by applying reduced pressure.The result is the clear to slightly turbid oil 1 having a viscosity of430 mPa·s and a amine number of 0.23.

PREPARATION EXAMPLE 2

693.75 g of an OH-terminal polydimethylsiloxane having a viscosity of 50mPa·s are mixed with 21.38 g ofaminoethylaminopropylmethyldimethoxysilane, 358.07 g of polyethyleneglycol 400 and a basic catalyst. The result is a turbid whitish mixture.The mixture is heated gradually to 200° C. with stirring, in the courseof which volatile constituents are removed by applying reduced pressure.After cooling to 60° C. and aeration, 10.10 g of succinic anhydride areadded to the oil. After 90 minutes the yellow oil 2 is obtained, havinga viscosity of 702 mPa·s and an amine number of 0.12.

PREPARATION EXAMPLE 3

555.00 g of an OH-terminal polydimethylsiloxane having a viscosity of 50mPa·s are mixed with 17.10 g ofaminoethylaminopropylmethyldimethoxysilane, 573.60 g of polyethyleneglycol 400 and a basic catalyst. The result is a turbid whitish mixture.The mixture is heated gradually to 200° C. with stirring, in the courseof which volatile constituents are removed by applying reduced pressure.The result is the clear to slightly turbid oil 3 having a viscosity of209 mPa·s and a amine number of 0.17.

PREPARATION EXAMPLE 4

555.00 g of an OH-terminal polydimethylsiloxane having a viscosity of 50mPa·s are mixed with 17.10 g ofaminoethylaminopropylmethyldimethoxysilane, 573.60 g of polyethyleneglycol 400 and a basic catalyst. The result is a turbid whitish mixture.The mixture is heated gradually to 200° C. with stirring, in the courseof which volatile constituents are removed by applying reduced pressure.After cooling to 60° C. and aeration, 8.00 g of succinic anhydride areadded to the oil. After 90 minutes the yellow oil 4 is obtained, havinga viscosity of 249 mpa·s and an amine number of 0.09.

COMPARATIVE EXAMPLE EXAMPLE 5

A mixture of 967 g of OH-terminal polydimethylsiloxane having aviscosity of about 70 mpa·s at 25° C., 33 g ofaminoethylaminopropyldimethoxymethylsilane and a 40% strength solutionof a quaternary ammonium hydroxide in methanol is heated at 80° C. undernitrogen and with stirring for 4 hours. The quaternary ammoniumhydroxide is then deactivated by heating at 150° C. for 60 minutes andapplying reduced pressure and at the same time the organopolysiloxane isfreed from constituents which boil under these conditions. The resultingorganopolysiloxane has a viscosity of 1000 mPa·s at 25° C. and atitratable amine content of 0.3 ml of 1 N HCl/g of solids (oil 5).

USE EXAMPLE (UE)

20 parts of oil 1 are stirred in 80 parts of water which has beenacidified to a pH of 3 with acetic acid. A slightly turbid dispersion isobtained (UE1).

20 parts of oil 2 are stirred in 80 parts of water. A slightly turbiddispersion is obtained (UE2).

20 parts of oil 3 are stirred in 80 parts of water which has beenacidified to a pH of 3 with acetic acid. A clear solution is obtained(UE3).

20 parts of oil 4 are stirred in 80 parts of water. A clear solution isobtained (UE4).

4 parts of the emulsifier Genapol X060 (from Hoechst AG) and 4 parts ofwater are mixed homogeneously. 20 parts of oil 5 are then incorporatedslowly and in portions. Using 74.5 parts of water the homogeneousmixture is diluted, slowly at first and then rapidly. The emulsion isfiltered through fine Perlon fabric. Subsequently, 1.5 parts of aceticacid (concentrated) are added to the emulsion (UE5).

50 g each of UE1 to UE5 are mixed with 950 g of deionized water.Polyester/cotton fabric (poly/cotton) (65:35) is immersed thoroughly ineach mixture and squeezed off on a pad mangle (30 kg load). Thepoly/cotton fabrics F1 to F5 are dried at 150° C. for 5 minutes.

The hand is evaluated in accordance with a relative scale from 0-10,where the value 10 represents the best soft hand in each case.

The hydrophilicity of the fabric is defined by the time, measured inseconds, for one drop of water a) to start to wet the fabric and b) tobe absorbed completely by the fabric.

Hydrophilicity Time to start Absorption Fabric Soft hand of wetting [s]time [s] F1 8 1 7 F2 8 1 6 F3 6 1 3 F4 6 1 3 F5 10 50 156 Blank value 01 5

The result shows that the silicones oil 1 to oil 4 of the inventionmaintain outstandingly the absorbency of the fabrics treated with themand at the same give them a very good soft hand.

What is claimed is:
 1. A process for textile treatment comprisingcontacting a textile material with a composition comprising at least one(A) silane or organosiloxane having at least one monovalent SiC-bondedhydrocarbon radical having primary, secondary and/or tertiary aminogroups, and at least one (B) (iso)oxyalkyl radical which is attached tosaid silane or organosiloxane (A) via Si—O—C bonding, wherein thetextile material is not rendered hydrophobic by said contacting withsaid silane or said organopolysiloxane.
 2. The process of claim 1,wherein the (iso)oxyalkyl radical (B) is (OC_(n)H_(n)(—R))_(o), where Rcan be identical or different and denotes hydrogen or a methyl radical,n is 2, 3 or 4 and o is from 1 to
 100. 3. The process of claim 1, inwhich the silane or organosiloxane (A) contains at least one siloxaneunit of the general formula (I) $\begin{matrix}{R_{a}^{1}Q_{b}{SiO}_{\frac{({4 - a - b})}{2}}} & (I)\end{matrix}$

and all other siloxane units have the general formula (II)$\begin{matrix}{R_{c}^{1}{SiO}_{\frac{({4 - c})}{2}}} & ({II})\end{matrix}$

where R¹ denotes identical or different monovalent, unsubstituted orfluorine-, chlorine- or bromine-substituted C₁ to C₁₈ hydrocarbonradicals, hydrogen atoms, C₁- to C₂-alkoxy radicals, hydroxyl radicals,or alkyl glycol radicals, Q denotes a group of the general formula (III) —R²—[NR³(CH₂)_(m)]_(d)N(R³)₂  (III) where R² denotes a divalent C₁ toC₁₈ hydrocarbon radical, R³ denotes a hydrogen atom or an unsubstitutedor fluorine-, chlorine- or bromine- or C₁- to C₅-alkoxy-substituted C₁to C₁₈ hydrocarbon radical, a is 0, 1 or 2, b is 1, 2 or 3, c is 0, 1, 2or 3, d is 0, 1, 2, 3 or 4, m is 2, 3, 4, 5 or 6, and the sum of a and bis not more than
 4. 4. The process of claim 2, in which the silane ororganosiloxane (A) contains at least one siloxane unit of the generalformula (I) $\begin{matrix}{R_{a}^{1}Q_{b}{SiO}_{\frac{({4 - a - b})}{2}}} & (I)\end{matrix}$

and all other siloxane units have the general formula (II)$\begin{matrix}{R_{c}^{1}{SiO}_{\frac{({4 - c})}{2}}} & ({II})\end{matrix}$

where R¹ denotes identical or different monovalent, unsubstituted orfluorine-, chlorine- or bromine-substituted C₁ to C₁₈ hydrocarbonradicals, hydrogen atoms, C₁- to C₁₂-alkoxy radicals, hydroxyl radicals,or alkyl glycol radicals, Q denotes a group of the general formula (III)—R²—[NR³(CH₂)_(m)]_(d)N(R³)₂  (III) where R² denotes a divalent C₁ toC₁₈ hydrocarbon radical, R³ denotes a hydrogen atom or an unsubstitutedor fluorine-, chlorine- or bromine- or C₁- to C₅-alkoxy-substituted C₁to C₁₈ hydrocarbon radical, a is 0, 1 or 2, b is 1, 2 or 3, c is 0, 1, 2or 3, d is 0, 1, 2, 3 or 4, m is 2, 3, 4, 5 or 6, and the sum of a and bis not more than
 4. 5. The process of claim 1, in which the aminecontent of the composition is from 0.01 to 2 meq/g, measured as theconsumption of 1 N hydrochloric acid in ml/g by the composition (A) and(B) on titration to the neutral point.
 6. The process of claim 3, inwhich the amine content of the composition is from 0.01 to 2 meq/g,measured as the consumption of 1 N hydrochloric acid in ml/g by thecomposition (A) and (B) on titration to the neutral point.
 7. Theprocess of claim 4, in which the amine content of the composition isfrom 0.01 to 2 meq/g, measured as the consumption of 1 N hydrochloricacid in ml/g by the composition (A) and (B) on titration to the neutralpoint.
 8. A process for preparing the composition of claim 1, byreacting at least one (A) silane or organosiloxane which has at leastone monovalent SiC-bonded radical with primary, secondary and/ortertiary amino groups, with a glycol which has at least one (B)(iso)oxyalkyl radical.
 9. A process for preparing the composition ofclaim 2, by reacting at least one (A) silane or organosiloxane which hasat least one monovalent SiC-bonded radical with primary, secondaryand/or tertiary amino groups, with a glycol which has at least one (B)(iso)oxyalkyl radical.
 10. A process for preparing the composition ofclaim 3, by reacting at least one (A) silane or organosiloxane which hasat least one monovalent SiC-bonded radical with primary, secondaryand/or tertiary amino groups, with a glycol which has at least one (B)(iso)oxyalkyl radical.
 11. A process for preparing the composition ofclaim 4, by reacting at least one (A) silane or organosiloxane which hasat least one monovalent SiC-bonded radical with primary, secondaryand/or tertiary amino groups, with a glycol which has at least one (B)(iso)oxyalkyl radical.